TWI355384B - Method for preparing acid addition salts of polyac - Google Patents

Method for preparing acid addition salts of polyac Download PDF

Info

Publication number: TWI355384B
Authority: TW; Taiwan
Prior art keywords: acid; ethyl; bis; acetamide; methyl
Prior art date: 2003-02-28

Application number

TW093105174A

Other languages

English (en)

Chinese (zh)

Other versions

TW200504052A (en

Inventor

Kimiyuki Shibuya

Tadaaki Ohgiya

Takayuki Matsuda

Original Assignee

Kowa Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-02-28

Filing date

2004-02-27

Publication date

2012-01-01

2004-02-27 Application filed by Kowa Co filed Critical Kowa Co

2005-02-01 Publication of TW200504052A publication Critical patent/TW200504052A/zh

2012-01-01 Application granted granted Critical

2012-01-01 Publication of TWI355384B publication Critical patent/TWI355384B/zh

Links

239000002253 acid Substances 0.000 title claims abstract description 101
150000003839 salts Chemical class 0.000 title claims abstract description 69
238000000034 method Methods 0.000 title claims abstract description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 94
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 51
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 24
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 145
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 127
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 69
150000001875 compounds Chemical class 0.000 claims description 64
-1 oxy oxy group Chemical group 0.000 claims description 40
238000002360 preparation method Methods 0.000 claims description 40
125000004076 pyridyl group Chemical group 0.000 claims description 17
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 16
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 15
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 13
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
125000003386 piperidinyl group Chemical group 0.000 claims description 9
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
239000011976 maleic acid Substances 0.000 claims description 6
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 claims description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
239000001530 fumaric acid Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 2
GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 claims description 2
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 2
235000021355 Stearic acid Nutrition 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
235000003704 aspartic acid Nutrition 0.000 claims description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
239000004310 lactic acid Substances 0.000 claims description 2
235000014655 lactic acid Nutrition 0.000 claims description 2
229960002510 mandelic acid Drugs 0.000 claims description 2
229940098779 methanesulfonic acid Drugs 0.000 claims description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
235000006408 oxalic acid Nutrition 0.000 claims description 2
229940055726 pantothenic acid Drugs 0.000 claims description 2
235000019161 pantothenic acid Nutrition 0.000 claims description 2
239000011713 pantothenic acid Substances 0.000 claims description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 2
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
229960004889 salicylic acid Drugs 0.000 claims description 2
239000008117 stearic acid Substances 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
125000004149 thio group Chemical group *S* 0.000 claims 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
RIXGJIUERIGEAR-UHFFFAOYSA-N 2-sulfanylcyclohexa-2,5-diene-1,4-dione Chemical compound SC1=CC(=O)C=CC1=O RIXGJIUERIGEAR-UHFFFAOYSA-N 0.000 claims 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims 1
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 1
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
KQWLJXPRTSCUOO-UHFFFAOYSA-N aminoazanium;bromate Chemical compound [NH3+]N.[O-]Br(=O)=O KQWLJXPRTSCUOO-UHFFFAOYSA-N 0.000 claims 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 claims 1
229960002768 dipyridamole Drugs 0.000 claims 1
235000013399 edible fruits Nutrition 0.000 claims 1
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 claims 1
239000000174 gluconic acid Substances 0.000 claims 1
235000012208 gluconic acid Nutrition 0.000 claims 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
238000006467 substitution reaction Methods 0.000 claims 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 claims 1
150000007514 bases Chemical class 0.000 abstract 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 69
239000002585 base Substances 0.000 description 29
239000011541 reaction mixture Substances 0.000 description 27
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 24
238000005259 measurement Methods 0.000 description 23
239000013078 crystal Substances 0.000 description 22
238000005160 1H NMR spectroscopy Methods 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
238000002844 melting Methods 0.000 description 19
230000008018 melting Effects 0.000 description 19
238000000921 elemental analysis Methods 0.000 description 16
239000000203 mixture Substances 0.000 description 16
239000000843 powder Substances 0.000 description 16
239000000243 solution Substances 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
238000001914 filtration Methods 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
238000012360 testing method Methods 0.000 description 11
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 10
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
238000000634 powder X-ray diffraction Methods 0.000 description 10
235000019439 ethyl acetate Nutrition 0.000 description 9
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 9
238000003756 stirring Methods 0.000 description 9
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
SJSWRKNSCWKNIR-UHFFFAOYSA-N azane;dihydrochloride Chemical compound N.Cl.Cl SJSWRKNSCWKNIR-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
101150041968 CDC13 gene Proteins 0.000 description 7
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000002904 solvent Substances 0.000 description 6
125000000446 sulfanediyl group Chemical group *S* 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
238000000113 differential scanning calorimetry Methods 0.000 description 4
239000012458 free base Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
206010003210 Arteriosclerosis Diseases 0.000 description 3
201000001320 Atherosclerosis Diseases 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VHTUJTDUGFVUGN-UHFFFAOYSA-N acetamide tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.C(C)(=O)N VHTUJTDUGFVUGN-UHFFFAOYSA-N 0.000 description 3
AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 description 3
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 3
229960002669 albendazole Drugs 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
208000011775 arteriosclerosis disease Diseases 0.000 description 3
239000012267 brine Substances 0.000 description 3
235000012000 cholesterol Nutrition 0.000 description 3
235000015165 citric acid Nutrition 0.000 description 3
229960004106 citric acid Drugs 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
230000007423 decrease Effects 0.000 description 3
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
238000004455 differential thermal analysis Methods 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
201000009925 nephrosclerosis Diseases 0.000 description 3
229960005489 paracetamol Drugs 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
238000003860 storage Methods 0.000 description 3
238000002411 thermogravimetry Methods 0.000 description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
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POAICWIBBFUQDX-UHFFFAOYSA-N tert-butyl n-[2,6-dimethyl-4-(trifluoromethyl)pyridin-3-yl]carbamate Chemical compound CC1=CC(C(F)(F)F)=C(NC(=O)OC(C)(C)C)C(C)=N1 POAICWIBBFUQDX-UHFFFAOYSA-N 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
238000012546 transfer Methods 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
238000004804 winding Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Epidemiology (AREA)
Urology & Nephrology (AREA)
Obesity (AREA)
Hematology (AREA)
Vascular Medicine (AREA)
Diabetes (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

TW093105174A 2003-02-28 2004-02-27 Method for preparing acid addition salts of polyac TWI355384B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2003052700		2003-02-28

Publications (2)

Publication Number	Publication Date
TW200504052A TW200504052A (en)	2005-02-01
TWI355384B true TWI355384B (en)	2012-01-01

Family

ID=32923406

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
TW100135167A TWI374136B (en)	2003-02-28	2004-02-27	Water adduct of acetamide moohydrochloride and its crystal
TW093105174A TWI355384B (en)	2003-02-28	2004-02-27	Method for preparing acid addition salts of polyac

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
TW100135167A TWI374136B (en)	2003-02-28	2004-02-27	Water adduct of acetamide moohydrochloride and its crystal

Country Status (21)

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US (2)	US7750150B2 (is)
EP (1)	EP1598346B1 (is)
JP (2)	JP4594863B2 (is)
KR (1)	KR101106127B1 (is)
CN (2)	CN1753886B (is)
AT (1)	ATE554083T1 (is)
AU (1)	AU2004215523B2 (is)
BR (1)	BRPI0407908A (is)
CA (1)	CA2516822C (is)
DK (1)	DK1598346T3 (is)
EA (1)	EA009045B1 (is)
ES (1)	ES2384517T3 (is)
IL (1)	IL170093A (is)
IS (1)	IS7978A (is)
MX (1)	MXPA05009129A (is)
MY (1)	MY140618A (is)
NO (1)	NO331272B1 (is)
NZ (1)	NZ541716A (is)
PL (1)	PL378292A1 (is)
TW (2)	TWI374136B (is)
WO (1)	WO2004076441A1 (is)

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* Cited by examiner, † Cited by third party
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TWI324600B (en) *	2003-07-07	2010-05-11	Kowa Co	2,4-bis (trifluoroethoxy) pyridine compound and drug containing the compound
RU2358734C2 (ru)	2003-08-29	2009-06-20	Кова Ко., Лтд.	Способ стабилизации бляшки с высоким содержанием липидов и способ профилактики ее разрушения
TW200619204A (en) *	2004-12-10	2006-06-16	Kowa Co	Method for reduction, stabilization and prevention of rupture of lipid rich plaque
RU2376300C1 (ru) *	2005-08-30	2009-12-20	Асахи Касеи Фарма Корпорэйшн	Сульфонамидное соединение
WO2008105058A1 (ja)	2007-02-27	2008-09-04	Asahi Kasei Pharma Corporation	スルホンアミド化合物
US7964613B2 (en) *	2007-02-28	2011-06-21	Asahi Kasei Pharma Corporation	Sulfonamide compound
WO2009004792A1 (ja) *	2007-07-02	2009-01-08	Asahi Kasei Pharma Corporation	スルホンアミド化合物及びその結晶
TWI619770B (zh) *	2007-11-30	2018-04-01	布勒岡股份有限公司	新穎的矽氧烷聚合物組成物
WO2011081118A1 (ja) *	2009-12-29	2011-07-07	興和株式会社	経口投与用医薬組成物
WO2011081117A1 (ja) *	2009-12-29	2011-07-07	興和株式会社	経口投与用固形医薬組成物
WO2011145340A1 (ja)	2010-05-19	2011-11-24	興和株式会社	非アルコール性脂肪性肝炎の予防及び／又は治療剤
MA46677A (fr) *	2015-06-17	2019-09-11	Gilead Sciences Inc	Co-cristaux, sels et formes solides de ténofovir alafénamide
WO2018092765A1 (ja) *	2016-11-15	2018-05-24	学校法人同志社	経鼻投与用医薬組成物

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IL112152A (en) *	1994-12-26	2000-11-21	Identa Ltd	Process and test kit for cocaine detection
ATE285402T1 (de) *	1997-05-26	2005-01-15	Kowa Co	Neue zyklische diaminverbindungen und heilmittel das diese enthält
US6969711B2 (en) *	1997-05-26	2005-11-29	Kowa Company, Ltd.	Cyclic diamine compounds and medicine containing the same
GB9826180D0 (en) *	1998-11-30	1999-01-20	Smithkline Beecham Plc	Novel process
US20060165605A1 (en) *	2001-12-28	2006-07-27	Ye-Mon Chen	Process to regenerate fcc spent catalyst
JP4745666B2 (ja) *	2002-12-12	2011-08-10	興和株式会社	ヒドロキシアルキル環状ジアミン化合物
TWI324600B (en) *	2003-07-07	2010-05-11	Kowa Co	2,4-bis (trifluoroethoxy) pyridine compound and drug containing the compound

2004
- 2004-02-25 MY MYPI20040608A patent/MY140618A/en unknown
- 2004-02-27 KR KR1020057015048A patent/KR101106127B1/ko not_active Expired - Fee Related
- 2004-02-27 EA EA200501379A patent/EA009045B1/ru not_active IP Right Cessation
- 2004-02-27 TW TW100135167A patent/TWI374136B/zh not_active IP Right Cessation
- 2004-02-27 PL PL378292A patent/PL378292A1/pl not_active IP Right Cessation
- 2004-02-27 EP EP04715495A patent/EP1598346B1/en not_active Expired - Lifetime
- 2004-02-27 AU AU2004215523A patent/AU2004215523B2/en not_active Ceased
- 2004-02-27 ES ES04715495T patent/ES2384517T3/es not_active Expired - Lifetime
- 2004-02-27 CN CN2004800052621A patent/CN1753886B/zh not_active Expired - Fee Related
- 2004-02-27 MX MXPA05009129A patent/MXPA05009129A/es active IP Right Grant
- 2004-02-27 CN CN201210189482.0A patent/CN102702171B/zh not_active Expired - Fee Related
- 2004-02-27 AT AT04715495T patent/ATE554083T1/de active
- 2004-02-27 TW TW093105174A patent/TWI355384B/zh not_active IP Right Cessation
- 2004-02-27 CA CA2516822A patent/CA2516822C/en not_active Expired - Fee Related
- 2004-02-27 NZ NZ541716A patent/NZ541716A/en not_active IP Right Cessation
- 2004-02-27 US US10/545,200 patent/US7750150B2/en not_active Expired - Fee Related
- 2004-02-27 WO PCT/JP2004/002375 patent/WO2004076441A1/ja not_active Ceased
- 2004-02-27 BR BRPI0407908-6A patent/BRPI0407908A/pt not_active Application Discontinuation
- 2004-02-27 DK DK04715495.0T patent/DK1598346T3/da active
- 2004-02-27 JP JP2005502951A patent/JP4594863B2/ja not_active Expired - Fee Related
2005
- 2005-08-04 IL IL170093A patent/IL170093A/en not_active IP Right Cessation
- 2005-08-12 IS IS7978A patent/IS7978A/is unknown
- 2005-09-02 NO NO20054100A patent/NO331272B1/no not_active IP Right Cessation
2010
- 2010-04-16 US US12/762,111 patent/US8518936B2/en not_active Expired - Fee Related
- 2010-07-15 JP JP2010160354A patent/JP5180998B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP1598346A1 (en)	2005-11-23
CA2516822C (en)	2012-09-25
NZ541716A (en)	2007-11-30
US8518936B2 (en)	2013-08-27
CN102702171A (zh)	2012-10-03
EA009045B1 (ru)	2007-10-26
KR101106127B1 (ko)	2012-01-20
EP1598346A4 (en)	2007-08-15
IS7978A (is)	2005-08-12
TW201202218A (en)	2012-01-16
MXPA05009129A (es)	2005-10-20
NO20054100L (no)	2005-09-22
AU2004215523A1 (en)	2004-09-10
TW200504052A (en)	2005-02-01
CN1753886B (zh)	2012-07-18
JPWO2004076441A1 (ja)	2006-06-01
IL170093A (en)	2012-02-29
US7750150B2 (en)	2010-07-06
AU2004215523B2 (en)	2009-07-16
WO2004076441A1 (ja)	2004-09-10
ES2384517T3 (es)	2012-07-06
CN1753886A (zh)	2006-03-29
BRPI0407908A (pt)	2006-02-14
MY140618A (en)	2009-12-31
KR20050105218A (ko)	2005-11-03
TWI374136B (en)	2012-10-11
ATE554083T1 (de)	2012-05-15
DK1598346T3 (da)	2012-05-29
JP5180998B2 (ja)	2013-04-10
US20060079688A1 (en)	2006-04-13
NO331272B1 (no)	2011-11-14
PL378292A1 (pl)	2006-03-20
CA2516822A1 (en)	2004-09-10
CN102702171B (zh)	2014-09-10
JP2010235635A (ja)	2010-10-21
US20100234599A1 (en)	2010-09-16
NO20054100D0 (no)	2005-09-02
JP4594863B2 (ja)	2010-12-08
EA200501379A1 (ru)	2006-02-24
EP1598346B1 (en)	2012-04-18

Publication	Publication Date	Title
US8518936B2 (en)	2013-08-27	Method for preparing acid addition salts of polyacidic basic compounds
US5786355A (en)	1998-07-28	4,6-diarylpyrimidine derivatives and salts thereof
NZ568289A (en)	2011-06-30	Polymorphs of (R)-3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-(1- piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine
JP2013139476A (ja)	2013-07-18	Ｎ−ヒドロキシ−３−［４−［［［２−（２−メチル−１ｈ−インドール−３−イル）エチル］アミノ］メチル］フェニル］−２ｅ−２−プロペンアミドの多形
TWI870440B (zh)	2025-01-21	活化素受體樣激酶抑制劑之鹽及晶體形式
CZ20014575A3 (cs)	2002-04-17	Nové deriváty piperazinylalkylthiopyrimidinu, farmaceutické kompozice je obsahující a způsob přípravy účinné látky
JPH02184673A (ja)	1990-07-19	スルホンアミド化合物
CZ420498A3 (cs)	1999-05-12	Indolinový derivát jako antagonista 5-HT-2C receptoru
JP4427249B2 (ja)	2010-03-03	新規デスロラタジン塩、その合成方法および医薬組成物
EP0257616A2 (en)	1988-03-02	Dihydropyridine derivates and pharmaceutical composition thereof
AU749575B2 (en)	2002-06-27	2-(3-(4-(2-T-butyl-6- trifluoromethylpyrimidin-4-yl) piperazin-1-yl) propylmercapto) pyrimidin-4-ol-fumarate
WO1995019345A1 (en)	1995-07-20	Diazacycloalkanealkylsulfonamide derivative
JP2524731B2 (ja)	1996-08-14	ヒドロキシインド−ルエステル化合物
JP3514784B2 (ja)	2004-03-31	アリールアミド誘導体
NZ544482A (en)	2008-05-30	2,4-BIS(trifluoroethoxy)pyridine compound and medicine containing the same
DK143750B (da)	1981-10-05	Analogifremgangsmaade til fremstilling af 1,2,3,4-tetrahydrois oquinoliner
WO2020188833A1 (ja)	2020-09-24	ビアリールアミド誘導体の製造方法
JPH04103572A (ja)	1992-04-06	４―フェニル―２―（１―ピペラジニル）ピリジン誘導体
KR20110115343A (ko)	2011-10-21	베포타스틴 니코틴산염의 결정형 및 이의 제조방법

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Date	Code	Title	Description
2016-10-01	MM4A	Annulment or lapse of patent due to non-payment of fees